HCID 20227417, compound → HCID 20227422, compound

To a solution of 12.3 g (60.5 mmole) of 3-(4-fluoro-3-methoxyphenyl)pyridine in a mixture of 160 ml of methanol and 20.2 ml of concentrated hydrochloric acid was added 1.6 g of platinum oxide. The resulting mixture was shaken under an atmosphere of hydrogen at an initial pressure of 50 psig for 7 hours. The reaction mixture was filtered, an additional 1 g of platinum oxide was added, and the mixture was shaken under hydrogen at a pressure of 50 psig for 2 hours. The reaction mixture was then filtered, and the bulk of the methanol was removed by evaporation in vacuo. The residual aqueous system was diluted with water, and the resulting aqueous solution was washed with ether and then basified with 100 ml of 10% sodium hydroxide. The basified mixture was extracted with diethyl ether, and the combined extracts were washed with saturated sodium chloride solution, dried (K2CO3) and evaporated in vacuo. This afforded 9 g (71% yield) of the title compound.

1. filtrationThe reaction mixture was filtered
2. additionan additional 1 g of platinum oxide was added
3. stirringthe mixture was shaken under hydrogen at a pressure of 50 psig for 2 hours
4. filtrationThe reaction mixture was then filtered
5. customthe bulk of the methanol was removed by evaporation in vacuo
6. additionThe residual aqueous system was diluted with water
7. washthe resulting aqueous solution was washed with ether
8. extractionThe basified mixture was extracted with diethyl ether
9. washthe combined extracts were washed with saturated sodium chloride solution
10. dry with materialdried (K2CO3)
11. customevaporated in vacuo

ORD record

ord-ff5179e98d40455ea4a86d5bfdba3dea

Source dataset

uspto-grants-1986_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04623728